Mille Miglia 2015: Esquire Drives The World's Most Epic Car Rally

Italy's annual 1000-mile rally, captured by camera.

Italy is a country best seen at illegal speeds and during four days in May, all traffic yields to the Mille Miglia, a 1000-mile rally from Brescia, to Rome and back, that honors the original endurance race that ran from 1927-1957. These days, the race is a blowout reenactment of the original, with hundreds of the world's rarest vintage cars making the route. We took a Jaguar and a camera along to catch every palm-sweating, police-escorting, fume-choking moment. Here are the highlights.

Advertisement - Continue Reading Below

2 of 19

Only vehicles that originally entered the race from 1927 through 1957 – back when the Mille Miglia was a sanctioned race before gruesome fatalities forced Italy to bury it – are eligible. This 1938 Fiat 1100 508 CS Coupe is waiting to queue for the start.

Advertisement - Continue Reading Below

3 of 19

Before the Mille begins, cars must enter the scrutineering stage where they're checked for period correctness. Needless to say, this 1936 Aston Martin Two-Liter Speed passed.

A few American cars on the official entry list, like this 1954 Lincoln Capri Sport Coupe, are a chromed, ripped denim counterweight to the Mille's almost exclusively European field.

Advertisement - Continue Reading Below

Advertisement - Continue Reading Below

6 of 19

The higher the car's number, the later it ran in the original Mille. New or old, not many cars can approach the grace of a 1957 BMW 507.

Advertisement - Continue Reading Below

7 of 19

Period dress, in everything from overalls to pre-WWII leather helmets and goggles, is common on the Mille. Since many of the cars are roofless, pint-sized and without full windshields, they're essential gear to surviving all 1000 miles.

Advertisement - Continue Reading Below

8 of 19

A young pilota in his family's 1928 Lancia Lambda Torpedo. Lucky, lucky kid.

Advertisement - Continue Reading Below

9 of 19

The Mille Miglia is not a museum with velvet ropes guarding dusty exhibits. It's a free, open invitation for everyone to get close to their dream cars. And everyone is respectful, or else this 1953 Jaguar XK 120 would never turn a corner.

Advertisement - Continue Reading Below

10 of 19

Once the second hand ticks, Mille drivers turn serious. This 1937 BMW 328 is off, followed closely by a 1937 Riley Lynx-Sprite.

Advertisement - Continue Reading Below

Advertisement - Continue Reading Below

11 of 19

While digital clocks, smartphones and GPS are allowed for the most discerning Mille participants, we appreciate the timeless elegance of classic stopwatches.

Advertisement - Continue Reading Below

12 of 19

The drive into San Marino – a landlocked country, like the Holy See, that claims to be the world's oldest state – is a castle floating in the sky.

For our ride, we took a 2016 Jaguar F-type R Coupe. While the steering wheel was on the wrong side (note the British plates), we soon acclimated to all 550 horsepower and the F-type's crackling, backfiring exhaust. Here we are in Siena.

Advertisement - Continue Reading Below

17 of 19

Few modern cars deserve admiration in the Mille like this Mercedes SLR McLaren Stirling Moss, a 217-mph tribute to the British racer who set an unbreakable record in the 1955 Mille Miglia with a 300SLR.

Advertisement - Continue Reading Below

18 of 19

Jaguar team drivers Ben Cussons and Alex Goy celebrate their finish with cold beers in a 1952 C-type.

Advertisement - Continue Reading Below

19 of 19

We finish the Mille riding in a Jaguar C-type for a quick 10 minutes. Even with the engine cooking our feet and bugs flying into our teeth, we could have enjoyed it for 1,000 miles.

A Part of Hearst Digital Media
Esquire participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer sites.